The Virgin Millionaire
by TG81
Summary: Edward Cullen, successful and handsome and a virgin. What happens when he goes to a matchmaker to find a spouse? My contest entry for the AwkWard contest. Rated M for awkward dry humping.


**The "AwkWard" Contest**

**Story Title: **The Virgin Millionaire

**Pen name: **Tampagirl81

**Disclaimer: **No copyright infringement, blah blah blah.

_To see other entries in the "AwkWard" contest, please visit the C2:_

www(dot)fanfiction(dot)net/community/AwkWard_Contest/78356/

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I sat in the lobby staring at all the pictures of happy couples, some of which were holding babies. It filled my heart with hope that maybe one day soon that could be me and my future wife. Esme Platt was supposed to be one of the best in the field, with her brutal honesty and no-nonsense attitude. I looked down at my outfit, hoping that khaki pants and a green polo weren't too casual.

"Edward?" My head snapped toward the voice calling my name.

"That's me." I stood up and walked over to a tall, statuesque blonde.

"Hi, I'm Rosalie." She gave me a warm smile and shook my hand with a firm grip. "Today," she continued as she led me through the office, "you are going to tape a three minute video telling us about yourself. Please include your net worth as well as what you are looking for in your future spouse."

I gulped and nodded. "Will I be meeting with Esme today?"

"Yes. She will meet with you this afternoon at your home."

"Okay."

Rosalie led me to a small blue room with a video camera set on a tripod. She instructed me to sit on a couch directly in front of the camera and to start speaking whenever I saw the red light on the camera turn on.

I saw the light come on and froze. _How do I describe myself and what I want in under a few minutes? _I had fucking stage fright to a woman I would be meeting later anyway.

"Uhm," I cleared my throat, "I'm Edward Cullen, age twenty-eight. I'm originally from Chicago but moved to Seattle right after college. I'm in real-estate but I started out as a financial analyst. My net worth is roughly eight point seven million but changes on a daily basis depending on the market." I paused not remember what else I was supposed to say.

"What are you looking for, Edward? Why are you here?" Rosalie prompted me.

"I'm here because I want to find the love of my life. I've been so busy and I didn't even realize what my life was missing until a year or so ago. I want to eventually get married and have a family."

"What kind of girls do you like?"

I felt my face flush with embarrassment. I was afraid this would happen. I ran my hands through my hair in a failed attempt to calm my nerves. "Uhm, I'm not entirely sure."

"Well," Rose started with tight smile, but I could tell that she was getting frustrated with me by her tone. "The other girls you've been with before, what were they like?"

"I've never been with a woman before" I whispered, avoiding eye contact.

"EMMETT!" Rosalie yelled, throwing her clipboard at the wall, papers going everywhere. "I can't take this anymore!"

All of a sudden a large guy came rushing into the room. "What's going on, Rosie?"

"Another one! Do you do this to me on purpose?"

"What are you talking about?" he asked almost _too_ innocently.

"You son of a bitch! You purposely gave me another virgin! Is this your idea of a sick joke?" she yelled.

Well, fuck. This was awkward.

"I'm just gonna go now." I stood up and headed for the door. I had made my way to the revolving glass door of the lobby when I heard a fast-paced clicking coming from behind me.

"Mr. Cullen!" A woman's voice called out.

I slowly turned around and looked around but didn't see anyone until I looked down. A small dark haired girl was staring at me. "Mr. Cullen," she said more calmly, "I'm Alice Brandon, Esme's personal assistant. Please let me apologize for Rose and Emmett's behavior back there. It was entirely unprofessional and I can assure you that they will be dealt with in a proper manner. I can promise you that if you come back upstairs we can finish the video interview and get a matched up."

"No thank you." I turned and moved towards the front door.

"Please, I promise you'll deal with me only and-"

"Miss Brandon?" I asked. She nodded. "I appreciate your concern, but I'd rather be single if it means dealing with your office."

"Please, Mr. Cullen, we'll waive your fee into the club and give you a discount on next year's membership if you are still available at the time," she pleaded.

"I appreciate your offer, but no thank you."

"Can I set you up with someone outside of our club?"

"What?" I was utterly confused.

"My roommate, Bella. She's single and pretty and in a similar situation." She not-so-subtly eyed my crotch then looked up at me and winked.

"I don't think so." I shook my head and started to wonder how Esme got her reputation for being a brilliant matchmaker when she had a team a fuck-ups as her staff.

"Here's her picture." Alice thrust her iPhone in my face. The picture of the girl was gorgeous. She had long brown or black hair, it was difficult to tell, but she had large brown eyes and a tiny, but curvy figure.

"I don't know, Alice. Isn't this against company policy or something?" I asked. I found myself running my fingers through my hair.

"Probably, but we don't really follow company policy that much," she stated as if it were the most obvious thing in the world.

"Can I at least pass along your information to her and vice versa? I promise she's a very sweet girl and you'll adore her." She was now bouncing on her feet in anticipation, almost as if she knew I would agree.

"Fine," I relented.

"Oh, thank you, Mr. Cullen!" She reached up and gave me a tight hug.

"I think you can call me Edward at this point."

"I promise you won't regret this Edward. I will email you her information within the hour. Please don't let Emmett and Rose deter you."

I nodded. I left the building the threw myself in the back of the car. "You okay, Edward?" Jake, my driver, asked.

"I'm not entirely sure what the hell just happened, but yeah. I think I'll be okay." The past thirty minutes had been surreal. I had gone in hoping for a date to meet my soulmate and walked out with a potential date. Despite the way things had gone, everything worked out as planned.

--

I sat looking at the bar looking at my clock on my phone. She was already ten minutes late.

True to Alice's word, not even forty-five minutes after I left Esme's office I had an email with Bella Swan's email, phone number and two more pictures attached. I wondered if Bella knew how intrusive her roommate was. I had called her later that evening and she seemed like a nice enough girl. She was a college student and was trying to make it as a writer. After we had talked for almost an hour, she hesitantly agreed to meet me for dinner the next night.

So here I was, sitting alone at a five-star restaurant bar waiting for my date. I decided to leave and called Jake to bring the car around so that I could leave. He informed me that he was already out front.

I threw a couple bills on the bar to cover my tab and Bella's untouched drink and left. I walked outside to see Jake and a girl in a form fitting black dress and heels chatting and laughing. Upon closer inspection I saw that the girl he was talking to looked a lot like Bella. I felt a lump form in my throat. Could this date have gotten any worse?

"Jake," I snapped.

"Oh shit. Edward, I'm so sorry. You wouldn't believe this, but this is my friend Bella. We haven't seen each other in ages," he looked apologetic as he rambled. He didn't know the reason why I was here or the fact he had been flirting with my date. I suppose it didn't matter now, she clearly wasn't the type of person I was looking for.

Bella glanced down at her watch and the smile was erased from her face. "Shit, Jake. I gotta go. I was supposed to meet someone in there ten minutes ago. God, I hope he doesn't hate me," she muttered her last few words.

"I think you were supposed to meet me." My words came out more harsh than I intended.

"Edward?" She glanced from Jake to me and back to Jake, I could see her mind working as she was piecing things together. "I'm so sorry." She stuck her hand out. "I ran into Jake and we got to talking and catching up and I lost track of time. I promise I'm not usually flaky." Her cheeks flushed with embarrassment.

"It's my fault, boss. I promise." Jake looked apologetic.

After thinking for a few seconds I decided to let it go. If they really were childhood friends then there wasn't anything I could do about it. "Bella, I believe they still have our reservation if you would care to join me for dinner?" I asked in a softer tone.

"I would love to, Edward." The smile she gave me melted away the last of my resolve. She took my arm as we turned back toward the restaurant bar. "Tell Billy I said 'hi'," she called out over her shoulder.

"Will do, Bells," Jake called back.

After the host led us to our table we sat in silence. The waiter came and we both ordered a glass of wine. When he brought our glasses with both ordered and continued to sit in silence.

"Can I ask you a personal question?" Bella asked with a bit of hesitation.

I nodded as I took a sip of wine.

"Is it true you're a virgin?"

I choked on my drink, causing it to spray out of my nose and on the table and Bella. "Excuse me?" I sputtered.

"Oh god! I'm so sorry. It just came out."

"That's what she said," we chuckled at the same time.

She grinned at me and grabbed her napkin, dabbing it across her chest. Oh sweet Jesus. I could feel my pants growing tighter as she continued to unknowingly molest her chest.

"Yes, it's true," I said softly.

She stopped what she was doing and stared.

"How is that possible?" she blurted out. She shook her head and continued, "I'm mean look at you. You're gorgeous, smart, you own a business _and_ you sit on the board of a successful NPO, not to mention you're a nice guy, so how does something like that happen, or not happen?"

I thought for a minute before I answered. I debated on whether or not I should give her my stock answer of waiting for the right person, even though it was only partially true.

"How do you know I'm a nice person?" I asked instead.

"I was late to meet you, although if I hadn't run into Jake, I would have been on time. Then the way you saw us talking, I could only imagine you would think the worst of me, but yet here we are." She waved her hand in the air.

She had a point.

"I could say the same things for you."

"I'm not a virgin, I haven't been for a long time." She shrugged.

I felt a lump form in my throat again. Was this supposed to be some kind of joke on me?

Suddenly her eyes grew wide at her admission. "Oh that's not what I meant! I took horseback riding lessons when I was a teenager. This is so awkward."

I nodded in agreement.

"Can we please just start over?" She must have seen the doubtful look on my face, so she added, "Please?"

I felt reluctant to agree but there was something about Bella that I wanted to know more about. I reached my hand over the table and reintroduced myself. "Hi, I'm Edward Cullen."

She shook my hand and grinned at me, "I'm Bella Swan."

For the next two hours we got to know each other over wine that wasn't snorted or spilled and an amazing meal. I learned more about Bella than I had ever expected and revealed more about myself than I had anticipated. I found myself becoming intrigued by Bella and knew that I didn't want the night to end. I asked if she would like see me again and she immediately agreed.

I walked her to her car and gave her a kiss that was intended to be chaste but quickly grew in intensity. As she moved her lips against mine she grabbed my shirt and pulled me closer to her body. I couldn't help but groan in reaction to her chest pressed against mine.

I'm still not entirely sure what came over me as I thrust my hips towards her and was met with a throaty moan. She felt so good and so _right_ pressed against me and I got the feeling that I had been waiting for, she would be the one.

"Edward," she murmured against my mouth.

"Hmm?" I murmured back.

"We should stop." I knew she was right but I didn't want to.

"I know," I agreed, but we didn't. Instead she ground her pelvis into mine even harder, creating a delicious friction that was going to end in at least one of us needing a change of clothing.

A few more minutes of kissing and grinding was starting to bring me very close to the edge. "Bella, if we don't stop, I'm going to-" I started to warn her.

"Do it," she said. She slid her hand from my shoulders to my ass and took a firm grab. She pushed my erection even closer to her, knowing that only a few layers of fabric were keeping us apart from actually having sex is what pushed me over the edge. The coil that had tightened above my cock released itself and I felt my crotch suddenly become warm and wet as I came.

"That was," I panted.

"Amazing," she finished. I leaned my forehead against hers and nodded. "Are you okay?" she giggled.

"Better than," I chuckled. I suddenly panicked. What if this wasn't what she wanted? She didn't get any relief and I wasn't sure if women could get blue balls too, but she had to be uncomfortable in someway.

"I hope you don't think bad of me, but I would really like to see you again. Not because of this," I gestured to my pants. "I really enjoyed spending this evening with you."

"I would really like that."

"Can I call you tomorrow?" I asked.

"I hope you do."

"Well...I should go get cleaned up..." I let my voice trail off, not wanting to let her go.

"Yeah," she agreed.

"Tomorrow, I promise I'll call you."

"Okay." I opened her truck door for her and watched her drive away.

I shifted and adjusted myself before I walked back around to meet Jake.

Jake took one glance at me and grinned. He opened my door as I slid in. He started to say something but I shook my head. "If you want a job tomorrow, you'll keep your mouth shut."

"Yes sir." He grinned at me.


End file.
